Pheromones are finding increasing acceptance as useful tools in pest control since they have been proven to be effective in disrupting the mating and reproductive cycles of specifically targeted insect species. In general, common pheromones are 10- to 18-carbon atom-containing olefins having a terminal alcohol, aldehyde or acetate functional group and possess a particular stereo-isomerism. A good example of a commercially viable pheromone is gossyplure, which is effective in controlling pink bollworm. Gossyplure comprises a mixture of 7,11-hexadecadienyl acetate stereoisomers, and a wide variety of synthesis routes to obtain this pheromone have been proposed. See, for example, U.S. Pat. Nos. 3,919,329, 3,996,270 and 4,296,042. A particularly simple synthesis route involves the disproportionation of 1,5-cyclooctadiene and 1-hexene in the presence of a disproportionation catalyst to yield the precursor 1,5,9-tetradecatriene (TDT) and other olefins, the TDT being subsequently converted to gossyplure. See, U.S. Pat. Nos. 4,609,498 and 4,654,461. However, to date this synthesis route has not been commercially attractive by virtue of its ability to produce but a single pheromone precursor and because of the low yields and selectivity obtained.
What is needed therefore is a simple method of synthesizing a wide variety of pheromone compounds and precursors that produces high yields and selectivity, and that is capable of producing stable and reproducible stereoisomeric ratios of products. These needs and others are met by the present invention which is summarized and described in detail herein.